I think this question has an unnecessary conspiranoic tone... maybe nobody thought that you would get something embarrassing in a yearbook because a teacher would be careful not to jeopardize its employment; maybe someone did check but was not aware of the issues with blackface or did not make a connection, maybe in Canadian politics the scrutiny of private life is less intensive than in the USA (certainly there are few countries where absolutely everything about the private life of politicians can make the headlines..).
– SJuan76Sep 20 '19 at 8:54

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I suggest you either remove "racist" from your title or change it to "(allegedly) racist"
– GuranSep 20 '19 at 9:17

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@Guran: well, Trudeau himself said the photo(s) were racist. Frankly a better term would be "racially insensitive" since it's not clear Trudeau did out of malice rather than ignorance of how it could be perceived. (As an aside, is everyone else who stood by him in those photos racist too?) But I guess he didn't want to come across as half-apologising, so he just declared the act racist...
– FizzSep 20 '19 at 9:33

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@Fizz "controversial" might be the best term here.
– GuranSep 20 '19 at 10:24

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There are no racist photos of Trudeau. There are pictures of him wearing masquerade costumes, which weren't racist then, and are racist now to only a very small number of individuals. Why would they have been considered of any importance in the past?
– jamesqfSep 20 '19 at 17:03

1 Answer
1

Several commentators (e.g. Vice article) have pointed out that the current Canadian election campaign has featured pretty heavily opposition research. So the context in which these Trudeau photos were released is not accidental, especially since similar material was used against Trudeau's opponents recently.

On the other hand, little has been revealed insofar how the first photo of Trudeau was discovered. A bit more is known about the subsequent ones, the effort for which appears to have been squarely inspired by the first, and they came from varied sources. The 2nd photo was found by Canadaland, a blog which specializes in deep digs in politicians' past. They claim to have simply used the Wayback Machine to look for similar material.

Some more commentary in Vice:

Given that this story broke in TIME rather than a Canadian outlet, you have to wonder whether any media companies here turned the story down and what reasons they gave. You also have to wonder why it didn’t come in the 11 years Trudeau has been MP, the six years he has been leader of the Liberals, his first election campaign as leader four years ago, or his first term as prime minister.

(Though in CANADALAND, Robert Jago has perhaps the best explanation: “Because he was a lifelong celebrity, I’d no sooner look into his background than I would the backgrounds of Prince William or a Kennedy—people about whom all is apparently known.”)

TIME does say how they verified the material's authenticity, but not how they found it out in the first place.